CH650776A5 - Derives de la pyrimidine, leur procede de preparation et les compositions therapeutiques les contenant. - Google Patents
Derives de la pyrimidine, leur procede de preparation et les compositions therapeutiques les contenant. Download PDFInfo
- Publication number
- CH650776A5 CH650776A5 CH6818/81A CH681881A CH650776A5 CH 650776 A5 CH650776 A5 CH 650776A5 CH 6818/81 A CH6818/81 A CH 6818/81A CH 681881 A CH681881 A CH 681881A CH 650776 A5 CH650776 A5 CH 650776A5
- Authority
- CH
- Switzerland
- Prior art keywords
- diamino
- phenyl
- pyrimidine
- chloro
- phenoxy
- Prior art date
Links
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 6
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title claims description 4
- 239000000203 mixture Substances 0.000 title description 33
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 76
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 38
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 33
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- -1 biphenyloxypropyl compound Chemical class 0.000 claims description 15
- 239000000460 chlorine Chemical group 0.000 claims description 15
- LVILGAOSPDLNRM-UHFFFAOYSA-N 4-methylpyrimidine Chemical compound CC1=CC=NC=N1 LVILGAOSPDLNRM-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000003230 pyrimidines Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
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- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 229910052740 iodine Chemical group 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- HERHQNVDSHUKAK-UHFFFAOYSA-N 6-methylpyrimidine-2,4-diamine Chemical compound CC1=CC(N)=NC(N)=N1 HERHQNVDSHUKAK-UHFFFAOYSA-N 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
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- 241000699670 Mus sp. Species 0.000 description 19
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- 229960000611 pyrimethamine Drugs 0.000 description 6
- WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
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- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 4
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YRULSMJTKCEWAX-UHFFFAOYSA-N 1-(3-bromopropoxy)-2-phenylbenzene Chemical class BrCCCOC1=CC=CC=C1C1=CC=CC=C1 YRULSMJTKCEWAX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- ZZORFUFYDOWNEF-UHFFFAOYSA-N sulfadimethoxine Chemical compound COC1=NC(OC)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ZZORFUFYDOWNEF-UHFFFAOYSA-N 0.000 description 2
- KXRZBTAEDBELFD-UHFFFAOYSA-N sulfamethopyrazine Chemical compound COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1 KXRZBTAEDBELFD-UHFFFAOYSA-N 0.000 description 2
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- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical class OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
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- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
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- 241000224017 Plasmodium berghei Species 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8034572 | 1980-10-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH650776A5 true CH650776A5 (fr) | 1985-08-15 |
Family
ID=10516909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH6818/81A CH650776A5 (fr) | 1980-10-27 | 1981-10-26 | Derives de la pyrimidine, leur procede de preparation et les compositions therapeutiques les contenant. |
Country Status (23)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4673677A (en) * | 1983-10-03 | 1987-06-16 | Pfizer Inc. | Method for treatment of gastrointestinal disorders |
| US4554276A (en) * | 1983-10-03 | 1985-11-19 | Pfizer Inc. | 2-Amino-5-hydroxy-4-methylpyrimidine derivatives |
| WO1992008461A1 (en) * | 1990-11-14 | 1992-05-29 | Protos Corporation | Specific inhibition of dihydrofolate reductase and compounds therefor |
| WO2002000683A2 (en) * | 2000-06-23 | 2002-01-03 | Vanderbilt University | Novel chain-breaking antioxidants |
| US8367669B2 (en) * | 2005-06-15 | 2013-02-05 | Vanderbilt University | Inhibitors of hemeprotein-catalyzed lipid peroxidation |
| US9133212B1 (en) | 2005-06-15 | 2015-09-15 | Vanderbilt University | Inhibitors of hemeprotein-catalyzed lipid peroxidation |
| SI2194985T1 (sl) * | 2007-10-08 | 2019-04-30 | Mmv Medicines For Malaria Venture | Protimalarijske spojine z gibkimi stranskimi verigami |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1546937A (en) * | 1976-07-29 | 1979-05-31 | Beecham Group Ltd | 2,4-diaminopyrimidine derivatives |
-
1981
- 1981-10-13 OA OA57517BISD patent/OA07362A/xx unknown
- 1981-10-21 US US06/313,493 patent/US4374136A/en not_active Expired - Fee Related
- 1981-10-21 ZA ZA817298A patent/ZA817298B/xx unknown
- 1981-10-21 NL NL8104766A patent/NL8104766A/nl not_active Application Discontinuation
- 1981-10-23 JP JP56168859A patent/JPS5799573A/ja active Pending
- 1981-10-23 GR GR66340A patent/GR75366B/el unknown
- 1981-10-23 AU AU76745/81A patent/AU547334B2/en not_active Ceased
- 1981-10-23 ZW ZW256/81A patent/ZW25681A1/xx unknown
- 1981-10-23 IE IE2498/81A patent/IE51670B1/en unknown
- 1981-10-24 KR KR1019810004070A patent/KR830007580A/ko not_active Ceased
- 1981-10-25 EG EG617/81A patent/EG15900A/xx active
- 1981-10-26 LU LU83713A patent/LU83713A1/fr unknown
- 1981-10-26 DK DK471181A patent/DK146067C/da not_active IP Right Cessation
- 1981-10-26 CH CH6818/81A patent/CH650776A5/fr not_active IP Right Cessation
- 1981-10-26 FR FR8120043A patent/FR2492821A1/fr active Granted
- 1981-10-26 BE BE0/206353A patent/BE890874A/fr not_active IP Right Cessation
- 1981-10-26 IL IL64123A patent/IL64123A/xx unknown
- 1981-10-26 PH PH26394A patent/PH17779A/en unknown
- 1981-10-27 IT IT24721/81A patent/IT1139562B/it active
- 1981-10-27 DE DE19813142559 patent/DE3142559A1/de not_active Withdrawn
- 1981-10-27 MA MA19515A patent/MA19313A1/fr unknown
-
1985
- 1985-12-30 MY MY556/85A patent/MY8500556A/xx unknown
-
1987
- 1987-01-27 KE KE3690A patent/KE3690A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR830007580A (ko) | 1983-11-04 |
| EG15900A (en) | 1987-10-30 |
| MY8500556A (en) | 1985-12-31 |
| IL64123A (en) | 1986-02-28 |
| AU547334B2 (en) | 1985-10-17 |
| IT1139562B (it) | 1986-09-24 |
| IE51670B1 (en) | 1987-02-04 |
| MA19313A1 (fr) | 1982-07-01 |
| AU7674581A (en) | 1982-05-06 |
| DK146067C (da) | 1983-11-14 |
| IE812498L (en) | 1982-04-27 |
| ZA817298B (en) | 1982-09-29 |
| DK146067B (da) | 1983-06-20 |
| FR2492821B1 (enrdf_load_stackoverflow) | 1985-02-01 |
| OA07362A (fr) | 1984-06-30 |
| KE3690A (en) | 1987-02-20 |
| DK471181A (da) | 1982-04-28 |
| FR2492821A1 (fr) | 1982-04-30 |
| LU83713A1 (fr) | 1982-05-07 |
| GR75366B (enrdf_load_stackoverflow) | 1984-07-13 |
| DE3142559A1 (de) | 1982-09-02 |
| NL8104766A (nl) | 1982-05-17 |
| IL64123A0 (en) | 1982-01-31 |
| JPS5799573A (en) | 1982-06-21 |
| IT8124721A0 (it) | 1981-10-27 |
| ZW25681A1 (en) | 1982-01-13 |
| PH17779A (en) | 1984-12-11 |
| US4374136A (en) | 1983-02-15 |
| BE890874A (fr) | 1982-04-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |